Impregnation sealants utilizing hydrosilation chemistry

ABSTRACT

This invention relates generally to heat curable compositions, particularly well utilized for use as impregnation sealants curable using hydrosilation chemistry. The heat curable compositions of the present invention can be stored and shipped as a one-part composition. The composition includes at least one curable unsaturated organic component, at least one co-reactant, which has at least two functional groups reactive with the organic component, and at least one catalyst of initiating the cure of the composition.

This application claims benefit of 60/205,954 May 19, 2000.

FIELD OF THE INVENTION

This invention relates generally to heat curable compositions,particularly well suited for use as impregnation sealants, curable usinghydrosilation chemistry.

BRIEF DESCRIPTION OF RELATED TECHNOLOGY

Impregnation sealing is commonly used to seal microporosity of a varietyof articles, structural components, and assemblies, such as, diecastings, electronic components, powder metal parts, fiber-reinforcedresin composites and the like. Impregnating articles with sealantsincreases its density, improves its strength and reduces corrosioninside the micropores of the article. Upon curing, the impregnatedarticles are capable of withstanding liquid and gas pressures duringuse. Microporosity in porous articles is particularly acute incomponents formed from metal powder and presents a significant obstaclein commercial end use applications, particularly when such porousarticles are employed in applications, such as fluid power systems andother liquid handling applications, as well as plating, coating andfurther processing.

Many porous articles are used commercially today, and manufactured froma wide variety of metals. Zinc, copper, iron, aluminum, brass andvarious other alloys are among the common metals to be sealed.

Conventional impregnation sealant compositions may be self-curinganaerobic sealants, thermal curing sealants and sealants which cure byboth anaerobic and heat cure mechanisms. Illustrative (meth)acrylatebased anaerobic impregnant sealant compositions are described in U.S.Pat. Nos. 5,618,857 issued to Newberth, III et al, and 3,672,942 issuedto Neumann et al, which are incorporated herein by reference. Heatcurable sealant compositions are described in U.S. Pat. No. 4,416,921issued to Dunn.

Although known commercial (meth)acrylate-based, impregnation sealantcompositions have many advantages to the end-users, the compositionshave a finite shelf life, which may be reduced if stored and/or shippedunder conditions of extreme beat. This becomes an issue due to thecommon practice of bulk storing and/or shipping the compositions in aready-to-use, one-part form, in which the curable portion (monomers) andthe cure initiating components are already mixed together.

There is a perception that exposure of one-part (meth)acrylate-basedsystems, as well as other free-radical initiated systems, to excessiveheat during transport can result in premature polymerization in thetransport tank. There is also a perception that such spuriouspolymerization could result in the generation of potentially dangerousamounts of heat. Though unlikely, such undesired spurious polymerizationmay be violent and could create potential environmental hazards. As aresult, there is also a perception that one-part (meth)acrylate-basedimpregnation sealant systems may stray from compliance with certain U.S.Department of Transportation (“DOT”) guidelines.

While the use of a two or multi-part composition, whereby the monomersand cure components are stored and/or shipped separately, alleviatespremature polymerization, it is less desirable from a cost standpointand end-user convenience standpoint, due to required additional trainingof and mixing by the end-user.

Accordingly, it would be desirable to provide an impregnation sealantcomposition that is shelf-stable at commonly encountered storage and/orshipping temperatures as a one-part composition, resisting prematurepolymerization, while still maintaining excellent viscosity and rapidcure characteristics.

SUMMARY OF THE INVENTION

The present invention provides such an impregnation sealant that can bestored and/or shipped as a one-part, heat curable composition thatresists premature polymerization.

In one aspect of the invention, there is provided a heat curablecomposition which includes at least one curable unsaturated organiccomponent, at least one co-reactant is provided-having at least twofunctional groups reactive with the organic component and at least onecatalyst capable of initiating cure of the composition.

In another aspect of the invention, there is provided an article ofmanufacture having an openable container for packaging the flowableinventive composition and the inventive sealant composition storedtherein

In yet another aspect of the present invention, there is provided amethod of manufacturing a heat curable composition of the presentinvention which includes providing at least one curable unsaturatedorganic component, combining the curable unsaturated organic componentwith at least one co-reactant having at least two functional groupsreactive with the organic component, and at least one catalyst capableof initiating cure of the composition.

The present invention also provides an article of manufacture having aporous surface which is impregnated with the inventive heat curablecomposition, and such article may be constructed of a metal, plastic orwood substrate and combinations thereof. The article may be anelectronic component.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a one-part curable composition thatovercomes the drawbacks of conventional sealant compositions.Specifically, the inventive sealant compositions are able to resistpremature polymerization so as to obviate the need for it to be storedas a two-part system. In fact, the inventive composition is capable ofbeing stored and shipped together as a one-part composition, i.e. itscurable organic component may be in contact with its co-reactant in asingle container. Thus, the compositions of the present invention avertthe concerns with the DOT shipping guidelines typically associated withconventional sealant compositions. Additionally, the sealant compositioncan be stored in a single ready-to-use package that will not requiremixing on the part of the consumer. The present invention provides theseadvantages while still retaining excellent sealant properties.

The composition of the present invention includes a curable unsaturatedorganic component, a co-reactant having at least two functional groupsreactive with the organic component and at least one catalyst. Othercomponents may also be added to the composition including but notlimited to other co-monomer species, reactive diluents, pigments,surfactants, fillers, polarization inhibitors, stabilizers,anti-oxidants, anti-corrosion additives and combinations thereof.

The curable unsaturated organic component of the present inventionserves as the primary component in the matrix of the composition Thiscomponent is preferably a non-silicon based cross-linkable monomer anddoes not contain alcohol or ester groups. The organic component isreactive with the co-reactant during hydrosilation. The curableunsaturated organic component employed in the impregnant sealantcomposition of the invention may be of any suitable type, and resinsincluding epoxies, phenolics, silicones, ally resins, vinyl resinssulfone resins, and combinations thereof. Particularly useful organiccomponents are allyl and vinyl resins such as vinyl stearate, allylmethacrylate, vinyl methacrylate and combinations thereof.

Additional useful allyl resins include allyl acetate, allylacetoacetate, allyl alcohol, allyl alcohol 1,2-butoxylate, allylamine,N-allylaniline, 4-allylanisole, allylbenzene, allyl 1-benzotrazolylcarbonate, ally benzyl ether, ally bromide,allyl-2-bromo-2-methylpropionate, allyl butyl ether, allyl butyrate,ally chloride, allyl chloroacetate, allyl chloroformate, allyl cyanide,ally cyanoacetate, allyl cyclohexanepropionate, 3-allylcyclohexanone,allylcyclohexylamine, allylcyclopentane, N-allylcyclopentylamine, allyldiethylphosphonoacetate, 4-allyl-1,2-dimethoxybenzene, 4-allyl-2,6-dimethoxyphenol, allyldiphenylphosphine, allyl disulfide, allylether, ally ethyl ether, allyl glycidyl ether, allyl1,1,2,3,3,3-hexafluoropropyl ether, 1-ally-3-2-hydroxyethyl 2-thiourea,o-allylhydroxylamine hydrochloride hydrate, 1-allylimidazole, allyliodide, allyl isocyanate, allyl isothiocyanate, allylmagnesium bromide,allylmagnesim chloride, allyl mercaptan, allyl methacrylate, allylcarbonate, 2-allyl-2-methyl-1,3-cyclopentanedione,2-allyl-6-methylphenol,3-allyl-5-[1-methyl-2(1H)pyridinylidene]rhodanine, ally methyl sulfide,2-allyloxybenzaldehyde, allyloxy-tert-butyldimethylsilane,(allyloxycarbonylmethyl)triphenylphosphonium iodide,4allyloxy-2-hydroxybenzophenone, 3-allylooxy-2-hydroxy-1-propanesulfonicacid, doium salt, 3-allyloxy-1,2-propanediol, allylpalladium chloridedimer, allylpentafluorobenzene, 2-allylphenol, allyl phenyl ether, allylphenyl sulfone, allylphosphonic dichloride, allyl propyl ether,3-allylrhodanine, allyl sulfide, allyl-1,1,2,2-tetrafluoroethyl ether,allyl tetraisopropylophosphorodiamidite, 2-(allylthio)benzimidazole,4-ally-3-thiosemicarbazide, 1-allyl-2-thiourea,allyl-2,4,6-tribromophenyl ether, allyltributyltin, allyltrifluoroacetate, allytriphenylphosphonium bromide,allyltriphenylphosphonium chloride, allyl(triphenylphosphoranylidene)acetate, allyltriphenyltin, and allylurea.

Additional vinyl resins that may be useful include vinyl acetate,vinylacetic acid, vinyl acrylate, 4-vinylaniline, 4vinylanisole,9-vinylanthracene, vinyl benzoate, 4-vinylbenzoic acid, vinylbenzylchloride, 4-vinylbenzyl chloride, 4-vinylbiphenyl, vinyl bromide, vinyl4-tert-butylbenzoate, 9-vinylcarbazole, vinyl chloride, vinylchloroformate, vinyl crotonate, vonylcyclohexane, 4-vinyl-1-cyclohexene,4-vinyl-1-cyclohexene, 4-vinyl-1-cyclohexene 1,2-epoxide,vinylcyclopentane, vinyl decanoate, 2-vinyl-1,3-doxolane, vinylenecarbonate, vinylene trithiocarbonate, vinyl 2-ethylhexanoate,vinylferrocene, N-vinylformamide, 4,4-vinylidenebis(N,N-dimethylaniline), vinylidene chloride, vinyldene fluoride,1-vinylimidazole, vinylmagnesium bromide, vinyl methacrylate,2-vinylnaphthalene, vinyl neodecanoate, 5-vonyl-2-norbornene,4-vonylphenylboronic acide, vinylphosphonic acid, N-vinylphthalimide,vinyl pivalate, vinyl propionate, 2-vinylpyridine, 4-vinylpyridine,1-vinyl-2-pyrrolidone, vinyl stearate, vinyl sulfone, vinylsulfonicacid, sodium salt, vinyltrifluoroacetate, and vinyltriphenylphosphoniumbromide.

The amount of the curable unsaturated organic component is from about 50to about 95% by weight, of total composition. Desirably, the amount isfrom about 80 to about 90% by weight, of the total composition.

Particularly useful organic components include glycidyl ether type epoxyresins such as bisphenol A type epoxy resins, bisphenol F type epoxyresins, phenol novolak type epoxy resins, orthocresol novolak type epoxyresins, brominated epoxy resins and biphenyl type epoxy resins, cyclicaliphatic epoxy resins, glycidyl ester type epoxy resins, glycidylaminetype epoxy resins cresol novolak type epoxy resins, naphthalene typeepoxy resins, phenol aralkyl type epoxy resins, cyclopentadiene typeepoxy resins, heterocyclic epoxy resins and combinations thereof Diallylether Bisphenol A is a particularly desirable organic component for useherein.

When monofunctional (meth)acrylate esters are employed in the sealantcomposition, an ester which has a relatively polar alcohol moiety may beused. Such materials are less volatile than low molecular weight alkylesters and, in addition, the polar group tends to provide intermolecularattraction in the cured polymer, thus producing a more durable seal. Thepolar group may be selected from the group consisting of labilehydrogen, heterocylic ring, hydroxy, amino, cyano, and halogen polargroups. Typical examples of compounds within this category arecyclohexylmethacrylate, tetrahydrofurfuryl methacrylate, hydroxethylacrylate, hydroxypropyl methacrylate, t-butylaminoethyl methacrylate,cyanoethylacrylate, and chloroethylmethacrylate.

The polymerizable poly(moth)acrylate esters are exemplified by, but notrestricted to, the following materials; di-, tri- andtetraethylenegylcol dimethylacrylate, dipropyleneglycol dimethacrylate;polyethyleneglycol dimethylacrylate; di(pentamethyleneglycol)dimethylacrylate; tetraethyleneglycol diacrylate; tetraethylenegylcoldi(chloroacrylate); diglycerol diacrylate; diglycerol tetramethacrylate;tetramethylene dimetacrylate; ethylene dimethacrylate; andneopentylglycol diacrylate.

The present invention uses at least one co-reactant having at least tworeactive functional groups, such as a silicon hydride with at least twoSiH groups in the molecule such that they react with the carbon-carbonmultiple bonds of the unsaturated organic component while in thepresence of the catalyst. The co-reactant should be present in amountssufficient to achieve the desired amount of crosslinking and desirablyin amounts of about 5 to about 50% by weight of the total composition.Desirably, the amount of co-reactant is about 15% by weight of the totalcomposition. A particularly useful co-reactant is polymethylhydrogensiloxane.

SiH functional co-reactants typically contain 2 or 3 hydrolyzable groupsconnected to the silicone atom thereof Desirably, there are three SiHgroups to encourage more cross-linking. The ratio of carbon double bondsin the organic component to SiH groups in the co-reaction is in therange of 1:2 to 1:3 and preferable 1:3 to insure more cross-linking withthe unsaturated organic component.

The silicone hydride co-reactant typically has the formulaR_(a)Si(X)_(4-n)wherein the R groups are the same or different andselected from the group consisting of hydrogen, C₁-C₁₂ alkyl, C₆-C₁₂aryl, C₇-C₈arylalkyl, C₇-C₁₈ alkylaryl, haloalky, haloaryl andmonovalent ethylenically unsaturated radicals, X is a hydrolyzablefunctionality selected from the group consisting of alkoxy, oximino,enoloxy, amino and amido and n is an integer of from 0 to 1, with theproviso that when x is alkoxy, the reaction is in the presence of anorgano lithium, titanium or tin catalyst, said silicone compositionhaving at least one silane per SiH functionality.

The silicon hydride co-reactant includes agents conforming to theformula below:

wherein at least two of R⁷, R⁸ and R⁹ are H; otherwise R⁷, R⁸ R⁹ can bethe same or different and can be a substituted or unsubstitutedhydrocarbon radical from C₁₋₂₀ such hydrocarbon radicals including thoseas previously defined for formula I above; thus the SiH group may beterminal, pendent or both; R¹⁰ can also be a substituted orunsubstituted hydrocarbon radical from C₁₋₂₀ such hydrocarbon radicalsincluding those as previously defined for formula I above, and desirablyis an allyl group such as methyl; x is an integer from 10 to 1,000; andy is an integer from 1 to 20. Desirably R groups which are not H aremethyl.

Silane compounds serve as useful monomers or capping agents for monomerswhose length, size, extent of branching in distribution of functionalgroups may be designed to provide specific desirable properties in theresulting curable polymer thereof. Examples of suitable hydrolyzablegroups include chloro, methoxy, ethoxy, oxine such as methyl, ethyl,ketoxinino, acetoxy, N-diackylamino and the like. For mostorganosiloxane polymerization or capping reactions, methoxy or chlorogroups are useful. Silane compounds useful as the co-reactant includemethylhydrogen polysiloxanes, methylhydrogen dimethylsiloxaneco-polymers, alkyl methyl polysiloxanes, bis (dimethylsilyl)alkanes andbis(dimethylsilyl)benzene. Specifically, the following silanes have beenfound to be useful: methyl trimethylmethoxysilane, vinyltrioxyiminosilane, phenyl trioxyiminosilane, methyl trienoxysilane,vinyl trienoxysilane, phenyl trienoxysilane, tetraethoxysilane andcombinations thereof.

Whereas conventional impregnation sealant compositions use afree-radical mechanism, a heat-cure initiator or an initiator systemhaving a redox polymerization initiator, the inventive compositions usehydrosilation chemistry to cross-link the curable unsaturated organiccomponent and the co-reactant having two reactive functional groups.Hydrosilation is an addition cure reaction where a composition isthermally cured by means of a catalyzed cross-linking reaction betweenthe multiple carbon bonds of the unsaturated organic component and theco-reactant. The use of this hydrosilation chemistry permits storage andshipping in a single container of one-part heat curable compositions.

Hydrosilation catalysts include any catalyst or precursor catalyst thatis capable of initiating the cure of the composition. Such catalystsinclude those based on transition metals of Group VIII-metals such asruthenium, rhodium, palladium, osmium, iridium and platinum, and thelike including complexes of these metals.

Any type of platinum catalyst compatible with the present invention maybe used. Their selection depends upon such factors as speed of thereaction required as well as expense, useful shelf-fife, useful pot-lifeand the temperature at which the cure reaction is to take place.

Platinum containing catalysts are useful in this invention and includechloroplatinic acid, chloroplatinic acid hexahydrate, complexes ofchloroplatinic acid with cis-divinyltetramethyldisiloxane, dichloro-bis(triphenylphosphine) platinum (II), cis-dichloro-bis (acetonitrile)platinum (II), dicarbonyldichloroplatinum (II), platinum chloride andplatinum oxide. Zero valent platinum metal complexes, such as Karstedt'scatalysts in chloroplatinic acid, may also be used. The reactions can becarried out alone or in solvents, which do not interfere withhydrosilations. Toluene, hexene, tetrahydrofuran, methylene chloride andbenzene are examples of suitable organic solvents. The catalyst may besolid platinum, deposited on a carrier such as charcoal or gammaalumina.

The hydrosilation catalysts may be used in any amount effective forthermal curing to occur. The catalyst may be utilized at levels at about10 ppm to about 30 ppm and more preferably about 20 ppm.

Other classes of catalysts include, in addition to organoplatinum andorganoplatinum complexes, organorhodium and platinum alcoholates.Complexes of ruthenium, palladium, osmium and iridium are alsocontemplated. The amount of this catalyst is not critical so long asproper crosslinking is achieved. Combinations of various precious metalor precious metal-containing catalysts are contemplated.

A solubilized platinum catalyst complex is also comtemplated. Usefulcatalyst and curing agent solutions include methyl hydrogen polysiloxanesolution with a 25% platinum-catalyst solution, cyclo tri(vinylmethylsiloxane) with a Pt(CO)₂Cl₂ solution and combinations thereof inamounts of 0.02-20% and desirably 0.02-5.0% by weight of the solution.

In order for the catalyst to function most efficiently in the dynamiccuring environment, it is important that it is inherently thermallystable or that its activity is inhibited to prevent too rapid a reactionor catalyst decomposition. A particularly useful catalyst inhibitor isacetylenic alcohol. Appropriate catalyst inhibitors that are suitable tostabilize the platinum catalyst include 1,3,5,7 tetravinyl-1,3,7tetramethylcyclotetrasilozane and its higher analogs such as vinylcyclic pentamer. However, other olefins that are stable above 165° C.may also be useful. These include maleates, fumarates and cyclicpentamers. It is also particularly described to use a catalyst thatremains soluble in the reaction medium.

The inventive compositions are suitably non-aqueous, i.e., substantiallywater-free, in character. The sealant composition's viscosity isdesirably from about 1 to about 1,000 centipoise and desirably isbetween about 5 and 500 centipoise. The most highly desirable range isfrom about 5 to about 150 centipoise. Viscosities higher than thoseindicated may make penetration of the sealant into the porous partdifficult or impossible and reduce the ease of dissolution; extremelylow viscosity sealants tend to “leak” from the part subsequent topenetration. In certain sealing situations where relatively large gapsare to be closed and relative slowness of dissolution can be tolerated,much higher viscosity sealants (e.g., 10,000-100,000 centipoises) may bedesirable. Surface tension of the sealant also can effect thesecharacteristics, but control of viscosity seems to be the more importantfactor. The ideal viscosity for any sealant will be a function of thesolubility of the sealant, the particular surfactant to be used, and thepore size of the porous part to be impregnated, and can be determinedeasily with a minimum of routine tests. Viscosity values are measured bythe Cannon-Fenske method.

The inventive compositions are useful in most impregnation applicationssuch as to seal an article with a pourous surface. The composition isparticularly useful in sealing porous metals, such as those used inelectrical components and electrical connectors. Other applicationsinclude sealing the porous surfaces of articles used in the automobileindustry, such as intake manifolds, engine blocks, power steering pumps,air conditioning housings and the like. The inventive compositions mayalso be useful in sealing non-metal articles such as porous woodproducts.

The composition may contain conventional additives, which can beintroduced into the composition during or after the hydrosilationprocess. Additives which may interfere with hydrosilation should beadded after cross-linking reaches the desired level. Examples of suchadditives are antioxidants, viscosity modifiers, pigments, waxes,antistatic agents, ultraviolet stabilizers, plasticizers, foamingagents, flame retardants and other appropriate processing aids. Suchadditives may include from about 0.1 to about 30 percent by weight basedon the weight of the sealant composition product. Useful additivesinclude calcium carbonate, silica, talc, titanium dioxide, carbon blackand the like.

Typical collating agents useful for the purpose to include materialssuch as 1,2-bis(3,5 di-tert-butyl-4-hyroxyhydrocinnamoyl) hydrazine andthe like. These agents may be incorporated in the composition prior toor after the hydrosilation. Useful amounts of chelating agent range fromabout 0.1% to about 5.0% by weight of the total composition.

In preparation of the compositions of the present invention, the curableunsaturated organic component is blended or mixed with the co-reactantand the catalyst Subsequently, the sealant composition is impregnatedinto the pores of the part to be sealed and then heated in order toeffect the cross-linking of the curable unsaturated organic component.

The following examples serve to illustrate the invention, without in anyway restricting its spirit and scope. All percentages throughout thespecification and claims are by weight of the total composition unlessotherwise indicated.

EXAMPLES

Inventive composition 1 was prepared by blending diallyl ether bisphenolA (85% by weight of the total composition) with polymethylhydrogensiloxane (15% by weight of the total composition). A small amount ofplatinum catalyst was added to the composition and stirred for 5minutes. To cure the composition, it was placed in an oven at atemperature of about 56° C. for a period of time of about 3 minutes andthen in an oven at a temperature of about 100° C. for a period of timeof about 10 minutes. The compositions were determined to be fullypolymerized. To test the impregnation characteristics of Composition 1,stainless steel disks with a density of 6.5 to 6.8 were used. Two diskswere impregnated with Composition 1 at a vacuum of 29.8 in. Hg. One diskwas submerged in Composition 1 for 10 minutes and the second disk wassubmerged in Composition 1 for 15 minutes. Subsequently, these diskswere heat cured in a 90-95° C. water bath. A third “control” disk wasnot impregnated with the sealant composition.

The disks were weighed three times: prior to impregnation, afterimpregnation and after heat curing. As shown in Table 1, since disk 1and 2 each retained the weight of the sealant, it is clear that theinventive composition works extremely well as a porosity sealant.

TABLE 1 POROSITY SEAL TESTING WITH INVENTIVE COMPOSITION 1 Sample*Weight Gain Leak Rate/minute Disk 1 0.20 grams 0 Disk 2 0.31 grams 0Disk 3 0 grams >4 liters (control) *Samples impregnated are stainlesssteel #316 disks with a density of 6.5-6.8.

To test the stability of the inventive compositions, the inventivecomposition is placed in a 1 liter polyethylene container and kept at120° F. for 7 days. Compositions that showed little or no degradation orpolymerization were determined to have good stability.

The invention being thus described, it will be clear to those skilled inthe art that the same may be varied in many ways. Such variations arenot to be regarded as a departure from the spirit and scope of theinvention and all modifications are intended to be included within thescope of the claims.

1. A heat curable composition comprising: (i) at least one curableunsaturated organic component, wherein said curable unsaturated organiccomponent is cured by hydrosilation; (ii) at least one co-reactanthaving at least two functional groups reactive with the organiccomponent; and (iii) at least one catalyst capable of initiating cure ofthe composition, wherein said co-reactant is selected from the groupconsisting of methyl trimethylmethoxysilane, vinyl trioxyiminosilane,phenyl trioxyiminosilane, methyl trienoxysilane, vinyl trienoxysilane,phenyl trienoxosilane, tetra ethoxysilane and combinations thereof. 2.The composition according to claim 1, wherein said curable unsaturatedorganic component is a non-silicon based cross-linkable monomer.
 3. Thecomposition according to claim 1, wherein said curable unsaturatedorganic component is an allyl resin.
 4. The composition according toclaim 1, wherein said curable unsaturated organic component is a vinylresin selected from the group consisting of vinyl stearate, vinyl(meth)acrylate and combinations thereof.
 5. The composition according toclaim 1, wherein said curable unsaturated organic component comprisesdiallyl ether bisphenol A.
 6. The composition according to claim 1,wherein said curable unsaturated organic component is in an amount fromabout 50% to about 95% by weight.
 7. The composition according to claim1, wherein said catalyst is a metallo hydrosilation catalyst.
 8. Thecomposition according to claim 1, wherein said catalyst is based on ametal selected from the group consisting of ruthenium, palladium,rhodium, osmium, iridium, platinum and combinations thereof.
 9. Thecomposition according to claim 1, wherein said catalyst is present inamounts from about 1 ppm to about 30 ppm.
 10. An article of manufacturecomprising: an openable container for packaging a flowable heat curablecomposition according to claim 1 in which said heat curable compositionis stored.
 11. A method of manufacturing a heat curable compositionaccording to claim 1, the steps of which comprise: a) providing at leastone curable unsaturated organic component wherein said curableunsaturated organic component is cured by hydrosilylation; and b)combining said curable unsaturated organic component with at least oneco-reactant having at least two functional groups reactive with theorganic component and at least one catalyst capable of initiating cureof the composition, wherein said co-reactant is selected from the groupconsisting of methyl trimethylmethoxysilane, vinyl trioxyiminosilane,phenyl trioxyiminosilane, methyl trienoxysilane, vinyl trienoxysilane,phenyl trienoxosilane, tetra ethoxysilane and combinations thereof. 12.An article of manufacture impregnated with a heat curable compositionaccording to claim 1, said article comprising a porous surface.
 13. Anarticle according to claim 12, wherein said article is selected from thegroup consisting of metal substrate, plastic substrate, wood substrateand combinations thereof.
 14. An article according to claim 12, whereinsaid article is an electrical component.
 15. A heat curable compositioncomprising: (i) at least one curable unsaturated organic component,wherein said curable unsaturated organic component is cured byhydrosilation; (ii) at least one co-reactant having at least twofunctional groups reactive with the organic component; and (iii) atleast one catalyst capable of initiating cure of the composition,wherein said curable unsaturated organic component comprises diallylether bisphenol A wherein said co-reactant is selected from the groupconsisting of methyl trimethylmethoxysilane, vinyl trioxyiminosilane,phenyl trioxyiminosilane, methyl trienoxysilane, vinyl trienoxysilane,phenyl trienoxosilane, tetra ethoxysilane and combinations thereof. 16.The composition according to claim 15, wherein said curable unsaturatedorganic component is in an amount from about 50% to about 95% by weight.17. The composition according to claim 15, wherein said catalyst is ametallo hydrosilation catalyst.
 18. An article of manufacturecomprising: an openable container for packaging a flowable heat curablecomposition according to claim 15 which said heat curable composition isstored.
 19. A method of manufacturing a heat curable compositionaccording to claim 15, the steps of which comprise: a) providing atleast one curable unsaturated organic component, wherein said curableunsaturated organic component comprises diallyl ether bisphenol A; andb) combining said curable unsaturated organic component with at leastone co-reactant having at least two functional groups reactive with theorganic component and at least one catalyst capable of initiating cureof the composition wherein said co-reactant is selected from the groupconsisting of methyl trimethylmethoxysilane, vinyl trioxyiminosilane,phenyl trioxyiminosilane, methyl trienoxysilane, vinyl trienoxysilane,phenyl trienoxosilane, tetra ethoxysilane and combinations thereof. 20.An article of manufacture impregnated with a heat curable compositionaccording to claim 15, said article comprising a porous surface.